Sodium borohydride → HCID 57537637, compound

HRID 1693745Notes

Reaction equation

HRID 1693745 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[C:9]([C:10](=[O:16])[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:8][C:7]([Br:17])=[CH:6][N:5]=1>CO>[NH2:3][C:4]1[C:9]([CH:10]([OH:16])[C:11]([N:13]([CH3:14])[CH3:15])=[O:12])=[CH:8][C:7]([Br:17])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57537502HCID 57537502, compound

Product 1

HCID 57537637HCID 57537637, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium borohydride (85.5 mg, 2.25 mmol) was added to methanol (5 mL) at 0° C. After 5 min, 2-(2-amino-5-bromo-pyridin-3-yl)-N,N-dimethyl-2-oxo-acetamide (408 mg, 1.50 mmol) in MeOH (15 mL) was added. After 1 h, the reaction was quenched by addition of saturated NH4Cl and the mixture was concentrated in vacuo. The residue was extracted with ethyl acetate, dried over Na2SO4 and purified by silica gel chromatography using DCM and MeOH to afford 2-(2-amino-5-bromo-pyridin-3-yl)-2-hydroxy-N,N-dimethyl-acetamide (234 mg, 57.1%) as a brown oily solid. The material was used in the next step. MS: m/z 274 (M+H+).

Workup

  1. waitAfter 1 h
  2. customthe reaction was quenched by addition of saturated NH4Cl
  3. concentrationthe mixture was concentrated in vacuo
  4. extractionThe residue was extracted with ethyl acetate
  5. dry with materialdried over Na2SO4
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-cbc77870c1844edaa56693d68e85566f
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

Loading…